Metal-free one-pot synthesis of 2-substituted benzimidazoles from N-aryl imines and TMSN3

Sujeet Gaware, Rana Chatterjee, Vasudevan Dhayalan, Rambabu Dandela

Research output: Contribution to journalArticlepeer-review

5 Scopus citations

Abstract

Iodine-catalysed efficient synthesis of 2-substituted benzimidazoles has been developed under aerobic condition. The one-pot oxidative cascade reactions of anilines, aldehydes and trimethylsilyl azide (TMSN3) lead to the benzimidazoles derivatives in the presence of tert-butyl hydroperoxide (TBHP). Iodine efficiently promoted the cross-coupling strategy to achieve the desired compounds via the sequential C[sbnd]H functionalization and cyclization. The present method features a greener approach, readily accessible reagents, broad substrate scope, high yields of the products, shorter reaction time and mild conditions.

Original languageEnglish
Article number154289
JournalTetrahedron Letters
Volume115
DOIs
StatePublished - 31 Jan 2023
Externally publishedYes

Keywords

  • 2-Substituted benzimidazoles
  • Gram-scale synthesis
  • Iodine promoted
  • Metal-free
  • TMSN

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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